Modification of the polar head group of acetyl glyceryl ether phosphorylation and subsequent effects upon platelet activation

K. Satouchi, R. N Pinckard, Linda M Mcmanus, D. J. Hanahan

Research output: Contribution to journalArticle

89 Citations (Scopus)

Abstract

A series of phosphoglycerides containing the same structural unit, 1-O-alkyl-2-acetyl-sn-glycerol, was prepared with the following polar head groups: -3-phosphoric acid (AGEPA), -3-phosphorylethanol (AGEPEt), -3-phosphorylethanolamine (AGEPE), -3-phosphoryl-N-monomethylethanolamine (AGEPMME), -3-phosphoryl-N,N-dimethylethanolamine (AGEPDME), and -3-phosphorylcholine (AGEPC). These compounds were synthesized primarily by phospholipase D modification of AGEPC. The characterization of these derivatives was achieved through thin layer chromatography, infrared spectrometry, gas-liquid chromatography, and combined gas-liquid chromatography-mass spectrometry. Their ability to induce irreversible aggregation and 50% secretion of serotonin from washed rabbit platelets was investigated. The latter secretory activity, expressed on a molar basis (60 s following platelet stimulation) was shown to be particularly sensitive to the nature of the polar head group as follows; AGEPA 8.3 x 10-7 M; AGEPE, 6.8 x 10-7 M; AGEPEt, 4.0 x 10-7 M; AGEPMME, 3.7 x 10-9 M; AGEPDME, 4.5 x 10-10 M; and AGEPC, 1.8 x 10-10 M. It was concluded that the polar head group of the various acetyl glyceryl ether phosphoglycerides had an important role in expressing the biological activity of this unique type of phosphoglyceride towards platelets. It appears likely that the recognition site (receptor site) on platelets is more reactive to the dimethylethanolamine or the quaternary ammonium base, choline, than to any of the other polar head groups under consideration.

Original languageEnglish (US)
Pages (from-to)4425-4432
Number of pages8
JournalJournal of Biological Chemistry
Volume256
Issue number9
StatePublished - 1981

Fingerprint

Glyceryl Ethers
Phosphorylation
Deanol
Platelet Activation
Glycerophospholipids
Platelets
Phosphorylcholine
Blood Platelets
Chemical activation
Liquid chromatography
Gas chromatography
Thin layer chromatography
Phospholipase D
Thin Layer Chromatography
Choline
Bioactivity
Ammonium Compounds
Gas Chromatography
Glycerol
Gas Chromatography-Mass Spectrometry

ASJC Scopus subject areas

  • Biochemistry

Cite this

@article{06a8d310616348c6ac81359e580be602,
title = "Modification of the polar head group of acetyl glyceryl ether phosphorylation and subsequent effects upon platelet activation",
abstract = "A series of phosphoglycerides containing the same structural unit, 1-O-alkyl-2-acetyl-sn-glycerol, was prepared with the following polar head groups: -3-phosphoric acid (AGEPA), -3-phosphorylethanol (AGEPEt), -3-phosphorylethanolamine (AGEPE), -3-phosphoryl-N-monomethylethanolamine (AGEPMME), -3-phosphoryl-N,N-dimethylethanolamine (AGEPDME), and -3-phosphorylcholine (AGEPC). These compounds were synthesized primarily by phospholipase D modification of AGEPC. The characterization of these derivatives was achieved through thin layer chromatography, infrared spectrometry, gas-liquid chromatography, and combined gas-liquid chromatography-mass spectrometry. Their ability to induce irreversible aggregation and 50{\%} secretion of serotonin from washed rabbit platelets was investigated. The latter secretory activity, expressed on a molar basis (60 s following platelet stimulation) was shown to be particularly sensitive to the nature of the polar head group as follows; AGEPA 8.3 x 10-7 M; AGEPE, 6.8 x 10-7 M; AGEPEt, 4.0 x 10-7 M; AGEPMME, 3.7 x 10-9 M; AGEPDME, 4.5 x 10-10 M; and AGEPC, 1.8 x 10-10 M. It was concluded that the polar head group of the various acetyl glyceryl ether phosphoglycerides had an important role in expressing the biological activity of this unique type of phosphoglyceride towards platelets. It appears likely that the recognition site (receptor site) on platelets is more reactive to the dimethylethanolamine or the quaternary ammonium base, choline, than to any of the other polar head groups under consideration.",
author = "K. Satouchi and Pinckard, {R. N} and Mcmanus, {Linda M} and Hanahan, {D. J.}",
year = "1981",
language = "English (US)",
volume = "256",
pages = "4425--4432",
journal = "Journal of Biological Chemistry",
issn = "0021-9258",
publisher = "American Society for Biochemistry and Molecular Biology Inc.",
number = "9",

}

TY - JOUR

T1 - Modification of the polar head group of acetyl glyceryl ether phosphorylation and subsequent effects upon platelet activation

AU - Satouchi, K.

AU - Pinckard, R. N

AU - Mcmanus, Linda M

AU - Hanahan, D. J.

PY - 1981

Y1 - 1981

N2 - A series of phosphoglycerides containing the same structural unit, 1-O-alkyl-2-acetyl-sn-glycerol, was prepared with the following polar head groups: -3-phosphoric acid (AGEPA), -3-phosphorylethanol (AGEPEt), -3-phosphorylethanolamine (AGEPE), -3-phosphoryl-N-monomethylethanolamine (AGEPMME), -3-phosphoryl-N,N-dimethylethanolamine (AGEPDME), and -3-phosphorylcholine (AGEPC). These compounds were synthesized primarily by phospholipase D modification of AGEPC. The characterization of these derivatives was achieved through thin layer chromatography, infrared spectrometry, gas-liquid chromatography, and combined gas-liquid chromatography-mass spectrometry. Their ability to induce irreversible aggregation and 50% secretion of serotonin from washed rabbit platelets was investigated. The latter secretory activity, expressed on a molar basis (60 s following platelet stimulation) was shown to be particularly sensitive to the nature of the polar head group as follows; AGEPA 8.3 x 10-7 M; AGEPE, 6.8 x 10-7 M; AGEPEt, 4.0 x 10-7 M; AGEPMME, 3.7 x 10-9 M; AGEPDME, 4.5 x 10-10 M; and AGEPC, 1.8 x 10-10 M. It was concluded that the polar head group of the various acetyl glyceryl ether phosphoglycerides had an important role in expressing the biological activity of this unique type of phosphoglyceride towards platelets. It appears likely that the recognition site (receptor site) on platelets is more reactive to the dimethylethanolamine or the quaternary ammonium base, choline, than to any of the other polar head groups under consideration.

AB - A series of phosphoglycerides containing the same structural unit, 1-O-alkyl-2-acetyl-sn-glycerol, was prepared with the following polar head groups: -3-phosphoric acid (AGEPA), -3-phosphorylethanol (AGEPEt), -3-phosphorylethanolamine (AGEPE), -3-phosphoryl-N-monomethylethanolamine (AGEPMME), -3-phosphoryl-N,N-dimethylethanolamine (AGEPDME), and -3-phosphorylcholine (AGEPC). These compounds were synthesized primarily by phospholipase D modification of AGEPC. The characterization of these derivatives was achieved through thin layer chromatography, infrared spectrometry, gas-liquid chromatography, and combined gas-liquid chromatography-mass spectrometry. Their ability to induce irreversible aggregation and 50% secretion of serotonin from washed rabbit platelets was investigated. The latter secretory activity, expressed on a molar basis (60 s following platelet stimulation) was shown to be particularly sensitive to the nature of the polar head group as follows; AGEPA 8.3 x 10-7 M; AGEPE, 6.8 x 10-7 M; AGEPEt, 4.0 x 10-7 M; AGEPMME, 3.7 x 10-9 M; AGEPDME, 4.5 x 10-10 M; and AGEPC, 1.8 x 10-10 M. It was concluded that the polar head group of the various acetyl glyceryl ether phosphoglycerides had an important role in expressing the biological activity of this unique type of phosphoglyceride towards platelets. It appears likely that the recognition site (receptor site) on platelets is more reactive to the dimethylethanolamine or the quaternary ammonium base, choline, than to any of the other polar head groups under consideration.

UR - http://www.scopus.com/inward/record.url?scp=0019497634&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0019497634&partnerID=8YFLogxK

M3 - Article

C2 - 7217088

AN - SCOPUS:0019497634

VL - 256

SP - 4425

EP - 4432

JO - Journal of Biological Chemistry

JF - Journal of Biological Chemistry

SN - 0021-9258

IS - 9

ER -